Sales, marketing and tech knowledge for wholesale brands and salespeople.

As the old saying goes, “sales is both an art and a science.” This applies to building your team too. You can look at past sales, backchannel for references and have your potential hires pitch you to get a pulse on the science (and you should!). The art, however, you’ve got dig a bit deeper for, and particularly with professional objection handlers you need some different angles.

Sales people see through BS, so don’t ask your road warriors the Silicon Valley mainstay Manhole Cover Question. Keep it in context, keep it light, and make it part of the conversation. Here are five out of the box questions from Handshake’s Director of Sales, Brandon Gracey, to pepper into your interviewing.

5 Great Interview Questions to Ask Sales Reps

Question 1: If you could only listen to one song for the rest of your life, what would it be and why?

This one toes the line of “too out there,” but I really like it, mostly because of the last word. A good sales person is prepared for everything they should anticipate, but you can’t anticipate everything. Sales people get asked questions they don’t see coming, and what this questions lets you see is how the handle the on the fly thought process of one of those unexpected ones. Bonus points if it’s this one, it’ll help with all that drive time!

Question 2: What do you spend your commission on?

I like this much better than “What do you do for fun?” or “What are you personal interests?” It’s the same basic question but it does a couple of things in addition. First, it sets the bar high. By asking “What do you spend your commission on?” what you’re saying is, “You’re going to make a lot of money here.” Secondly, and well related, it lets your candidate know that you’re on board with sales people making money. They got into this line of work for a lot of reasons; the challenge, the interactions, the acclaim…but really, they got into it for the money. You want to encourage that behavior, and this question does it. (Check out our series, “Cool Tech for Your Commission Check” for tech recommendations worth your hard-earned cash.)

Question 3: How do you interact with the most difficult person in your personal life?

Sales people have customers, and sometimes those customers are difficult. You can ask the standard “How do you handle a difficult” customer and get the candidate’s standard answer, but that won’t tell you how they handle difficult customers, it will tell you if they prepared for the interview. What you really want to get a read on is; “How is this rep going to handle a customer who’s not happy with their at once pricing, or is late for their next meeting while getting berated about pricing on this one. This questions really asks, “How do you deal with people you want to avoid, but can’t?”

Question 4: What did your day look like yesterday?

This will give you some insight into how they organize their days and relieves you of asking “How do you organize your day?” Outside sales reps manage themselves day to day so how they think about their daily approach is going to directly relate to how effective and productive they can be. This question opens up more too, so dig into their answers. “Why did you do X first?” “What did you leave out that you wish you could have gotten to?” Additionally, try opening up with this. It’s easy to lose the first 10 minutes of your hour-long interview on breaking the ice, and relaxing the situation. This bridges the gap between “who are you” and “let’s get started.”

Question 5: What’s the worst part of being in sales?

Is it the quota? Is it the windshield time? Competitors? Losing shelf space? Management? What the answer is matters, but not as much as how they view the role. Every job has is challenges, and as a good sales manager you’re going to want to know which ones your candidates struggle with the most when they become your sales reps.

Hope you’re able to try a few (if not all) of these questions in your next interview to help determine whether the sales rep is the right fit. At the very least, you’ve had an interesting conversation. Good luck!